diisopropyl 3'-O-benzoyl-6-N-benzoyl-2'-O-dimethoxytrityl-β-D-arabinoadenosin-5'-O-ylmethanephosphonate

Base Information

• Chemical Name: diisopropyl 3'-O-benzoyl-6-N-benzoyl-2'-O-dimethoxytrityl-β-D-arabinoadenosin-5'-O-ylmethanephosphonate
• CAS No.: 1357015-90-7
• Molecular Formula: C₅₂H₅₄N₅O₁₁P
• Molecular Weight: 956.001
• Mol file: 1357015-90-7.mol

Synonyms:diisopropyl 3'-O-benzoyl-6-N-benzoyl-2'-O-dimethoxytrityl-β-D-arabinoadenosin-5'-O-ylmethanephosphonate

Chemical Property of diisopropyl 3'-O-benzoyl-6-N-benzoyl-2'-O-dimethoxytrityl-β-D-arabinoadenosin-5'-O-ylmethanephosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of diisopropyl 3'-O-benzoyl-6-N-benzoyl-2'-O-dimethoxytrityl-β-D-arabinoadenosin-5'-O-ylmethanephosphonate

There total 4 articles about diisopropyl 3'-O-benzoyl-6-N-benzoyl-2'-O-dimethoxytrityl-β-D-arabinoadenosin-5'-O-ylmethanephosphonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 19.0%

benzoyl cyanide (613-90-1) + diisopropyl 6-N-benzoyl-β-D-arabinoadenosin-5'-O-ylmethanephosphonate (1357015-86-1) + 4,4'-dimethoxytrityl chloride (40615-36-9) → diisopropyl 3'-O-benzoyl-6-N-benzoyl-2'-O-dimethoxytrityl-β-D-arabinoadenosin-5'-O-ylmethanephosphonate (1357015-90-7) + C52H54N5O11P (1357015-93-0)

Guidance literature:

diisopropyl 6-N-benzoyl-β-D-arabinoadenosin-5'-O-ylmethanephosphonate; 4,4'-dimethoxytrityl chloride; With pyridine; silver trifluoromethanesulfonate; at 20 ℃; for 16h;

benzoyl cyanide; With triethylamine; In acetonitrile; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1016/j.bmcl.2011.11.040

Reference yield:

bis(2-propyl)-p-toluenesulfonyloxymethylphosphonate (35717-98-7) → diisopropyl 3'-O-benzoyl-6-N-benzoyl-2'-O-dimethoxytrityl-β-D-arabinoadenosin-5'-O-ylmethanephosphonate (1357015-90-7) + C52H54N5O11P (1357015-93-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 16 h / 0 - 20 °C

2.1: acetic acid / 16 h / 20 °C

3.1: pyridine; silver trifluoromethanesulfonate / 16 h / 20 °C

3.2: 16 h / 20 °C / Inert atmosphere

With pyridine; silver trifluoromethanesulfonate; sodium hydride; acetic acid; In N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2011.11.040

Reference yield:

6-N-benzoyl-2',3'-O-bis-tetrahydropyranyl-β-D-arabinoadenosine (1357015-83-8) → diisopropyl 3'-O-benzoyl-6-N-benzoyl-2'-O-dimethoxytrityl-β-D-arabinoadenosin-5'-O-ylmethanephosphonate (1357015-90-7) + C52H54N5O11P (1357015-93-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 16 h / 0 - 20 °C

2.1: acetic acid / 16 h / 20 °C

3.1: pyridine; silver trifluoromethanesulfonate / 16 h / 20 °C

3.2: 16 h / 20 °C / Inert atmosphere

With pyridine; silver trifluoromethanesulfonate; sodium hydride; acetic acid; In N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2011.11.040

upstream raw materials:

benzoyl cyanide

diisopropyl 6-N-benzoyl-β-D-arabinoadenosin-5'-O-ylmethanephosphonate

4,4'-dimethoxytrityl chloride

6-N-benzoyl-2',3'-O-bis-tetrahydropyranyl-β-D-arabinoadenosine

Downstream raw materials:

4-methoxy-1-oxido-2-pyridylmethyl 6-N-benzoyl-3'-O-benzoyl-2'-O-dimethoxytrityl-β-D-arabinoadenosin-5'-O-ylmethanephosphonate